Live Music Schedule, September 2026
Fall is on the way, but the music is still going strong. Join us at Lucca Osteria & Bar this September for live entertainment featuring soulful R&B, classic rock, jazz, Motown, acoustic favorites, and more. Pair it with our classic menu, seasonal specials, a well-made cocktail, and good company. Full September schedule below.
Please note: Patio seating is available upon request and is assigned on a first-come, first-served basis. Due to high demand for patio dining, tables occupied before 8pm will be required to order at least one main entrée and one beverage per person. We kindly ask that you limit your dining time to a maximum of two hours. We appreciate your understanding and hope you enjoy your evening.
September
Thursday, September 3 | 6:30–9:30PM
🎤 DIVA MONTELL Pop & Opera | Celine Dion, Donna Summer, Rihanna, Sarah Vaughan
DivaMontell.com
A powerhouse vocalist blending soulful pop hits with a touch of opera drama. Expect a little glamour and a lot of talent.
Friday, September 4 | 6:30–9:30PM
🎙 ROSS FAILLA Standards & ’60s–’70s Oldies | Dean Martin, Frank Sinatra, Tony Bennett
rossfailla.com | SwingingtheStandards.com
Classic crooner favorites and timeless standards for an easygoing Friday evening.
Saturday, September 5 | 6:30–9:30PM
🎸 CAVE DWELLERS ’60s & ’70s Rock
cavedwellerschicago.com
Turn back the clock with classic rock favorites from two unforgettable decades.
Thursday, September 10 | 6:30–9:30PM
🎸 JOE CANTAFIO Acoustic Rock | Beatles, CCR, Elvis, U2, Don McLean, The Who
Familiar acoustic favorites spanning generations of rock and roll.
Friday, September 11 | 6:30–9:30PM
🎶 VINTAGE DUO Rock, Country & Pop | Journey, Bon Jovi, Eagles, Doobie Brothers, Fleetwood Mac, Sheryl Crow
A feel-good mix of rock, country, and pop classics made for singing along.
Saturday, September 12 | 6:30–9:30PM
🎤 ACOUSTIC JUKEBOX CHICAGO Rock, Pop & Country | Eagles, Foo Fighters, Rolling Stones, Garth Brooks, Zac Brown Band, Queen
jamesandfriendsacoustic.com/acoustic-jukebox
An acoustic spin on rock, pop, and country favorites everyone knows.
Thursday, September 17 | 6:30–9:30PM
🎙 RANDY MCCALLISTER Swing, Sinatra & Soul | Bobby Darin, Frank Sinatra, Nat King Cole
randymccallistermusic.com
Classic crooner vibes with a soulful soundtrack of standards and swing.
Friday, September 18 | 6:30–9:30PM
🎶 POWERPLAY FYI TRIO Rock, Pop, Motown, Latin & Jazz | Stevie Wonder, Earth, Wind & Fire, Ed Sheeran
powerplayfyi.com | facebook.com/powerplayfyi
A versatile trio mixing genres, decades, and plenty of crowd favorites.
Saturday, September 19 | 6:30–9:30PM
🎤 GIL DELAPAZ DUO Latin & Italian Vocalists
A lively mix of Latin and Italian music perfectly suited for a Saturday night at Lucca.
Thursday, September 24 | 6:30–9:30PM
🎸 MD 80’S DUO ’80s & ’90s | Rick Springfield, Lenny Kravitz, Nirvana, Katrina & The Waves, Billy Idol, Michael Jackson
mikedangeroux.com
Two decades of unforgettable hits, from ’80s pop anthems to ’90s alternative rock.
Saturday, September 26 | 6:30–9:30PM
🎙 JEORGE HOLMES Classic Vocal Hits
jeorgeholmes.com
An evening celebrating the hits and unmistakable style of classic vocalists.
🥃 Special Ticketed Event
Monday, September 28 | 6:00–9:00PM
🎶 CHRIS FISHER Jazz, R&B, Motown & Blues | Michael Jackson, Prince, Stevie Wonder
Chris Fisher performs as part of Lucca’s Angel’s Envy Bourbon & Cigar Dinner, a special ticketed evening featuring bourbon, dinner, cigars, and live music.
This performance is part of the ticketed event. Learn more and purchase tickets.
